The second person is a higher risk for a big company and a lower risk for a smaller one*. And vice versa. While this cuts against conventional thinking, it helps to elucidate the difference between what Jeff Bezos calls the Day One Company and the Day Two Company.
The first person has a “Day One” mindset. The second person is often “Day Two.” Day One creates a healthy and constant fear about the future and instills urgency. “Day One” is exactly what it sounds like, meaning that you must make the right decisions, quickly, or you will screw up the future of the company.
“Day Two” is well, Day Two or as Mr. Bezos calls it, “stasis.”
The second individual in our hiring situation is closer to the Day Two trap because they usually do not make the foundational decisions. In many companies, in fact, that individual is left to clean up the mess caused by their bosses, who feign interest in the Day One idea and speak in slick tones and offer their “thumbs up” in “war rooms” designed to “foster urgency” all to mask the fact that they are often Day Three or Four people with nice looking glasses. (Of course there are many great bosses in companies of all sizes–provided they are Day One companies.)
Worse yet, in “rest of the week” companies people are usually promoted for being good cleaners instead of great creators. Once you get the hang of it, cleaning up also helps you avoid the messier business of thinking great thoughts to advance your career.
The Day One person–often a successful small business person with a track record–has avoided the Day Two trap because they have lived without the luxury of time. They owe their very success to their ability to be decisive and the recognition that every enterprise, ultimately, lives or dies by decisions made and actions taken.
(* This is because a smaller company frequently benefits from the systems thinking of a big company mindset provided it is annealed by Day One discipline. I define small business as anything under 500 people. Middle managers in this size of organization can be Day One all day and often are. The company grows from their inputs as a result.)